An eighty-question security questionnaire often yields less than a twenty-minute conversation. Not because the questions are bad, but because they are filled in by someone other than the person who actually knows, and because "yes" to "is data encrypted" carries almost no information.
Here are six questions that do produce something useful, and what to listen for in each answer.
1. Where does processing run, and which jurisdiction governs you?
Two questions asked as one, and they need separate answers.
A vendor can run its servers in Frankfurt and still be a US company. In that case the location of the data centre does not tell you which government can compel disclosure.
Usable answer: the processing region, the domicile of the contracting entity and whether a parent company sits in a different jurisdiction. Evasion: "we host in the EU".
2. What do you retain, for how long and can I configure it?
Ask separately about three things: conversation content, technical logs and attachments. They often have different retention periods.
Also ask what happens between deletion and permanent removal. At most services that gap is around thirty days.
Usable answer: a period for each category, and whether it can be configured per tier. Evasion: "no longer than necessary".
3. Is my input used for training, and does that differ by tier?
The second half matters most. At nearly every provider the answer differs between the free account, the business account and the API.
Push further: does the commitment cover only model training, or also human review and quality assurance? Those are different things, as set out in what "we don't train on your data" actually means.
Usable answer: an answer per tier, with a reference to where it sits in the contract. Evasion: "we do not train on customer data".
4. Who inside your organisation can access my data, and why?
Almost every provider has grounds to review conversations when abuse is suspected. That is not suspicious; it is normal, and it belongs in your assessment rather than outside it.
Usable answer: under what circumstances, by which role, with what approval and whether it is logged. Evasion: "access is strictly limited".
5. Who are your sub-processors, and am I notified of changes?
AI services often rely on other AI services. A tool that works on your PDFs may call a third party's model internally. That third party is then part of your chain.
Usable answer: a current list with role and location, plus a notification period and a right to object. Evasion: a list with no date on it.
